N-[(3R,4R,5S,6R)-2,5-dihydroxy-6-(hydroxymethyl)-4-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]acetamide

• ChemBase ID: 158880
• Molecular Formular: C14H25NO10
• Molecular Mass: 367.349
• Monoisotopic Mass: 367.14784601
• SMILES: [C@@H]1([C@H]([C@@H]([C@@H]([C@@H](O1)O[C@H]1[C@@H]([C@@H](OC([C@H]1NC(=O)C)O)CO)O)O)O)O)C
• Canonical SMILES: OC[C@@H]1OC(O)[C@H]([C@H]([C@@H]1O)O[C@@H]1O[C@@H](C)[C@H]([C@@H]([C@@H]1O)O)O)NC(=O)C
• InChI: InChI=1S/C14H25NO10/c1-4-8(18)10(20)11(21)14(23-4)25-12-7(15-5(2)17)13(22)24-6(3-16)9(12)19/h4,6-14,16,18-22H,3H2,1-2H3,(H,15,17)/t4-,6+,7+,8+,9+,10+,11-,12+,13?,14-/m0/s1
• InChIKey: TUXVLTYUDHJDAL-SFHUXEFOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(3R,4R,5S,6R)-2,5-dihydroxy-6-(hydroxymethyl)-4-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]acetamide
• IUPAC Traditional name: (GlcNAc)1 (LFuc)1
• Synonyms: 2-(Acetylamino)-2-deoxy-3-O-(6-deoxy-α-L-galactopyranosyl)-D-glucopyranose; Fuc1-α-3GlcNAc; 2-Acetamido-2-deoxy-3-O-(α-L-fucopyranosyl)-D-glucopyranose

Database IDs

• CAS Number: 52630-68-9
• PubChem SID: 162253015
• PubChem CID: 52921582

CALCULATED PROPERTIES

• Acid pKa: 11.509981
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -3.9445007
• LogD (pH = 7.4): -3.944533
• Log P: -3.9445002
• Molar Refractivity: 77.8943 cm^3
• Polarizability: 32.49977 Å^3
• Polar Surface Area: 178.17 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: >155°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A151500

Oligosaccharide which participates in cell adhesion between bacterial and eukaryotic cells

REFERENCES

• Perret, S., et al.: Biochem. J., 389, 325 (2005)
• Ma, B., et al.: J. Biol. Chem., 281, 6385 (2005)
• Ajisaka, K., et al.: J. Agric. Food Chem., 57, 3102 (2005)